Is there some kind of a timeout setting for Source Offsite. It seems that I lose my connection to SourceOffsite when I try to check out a file that has been loaded into Visual Studio for quite some time (several hours) I frequently get prompted, after a delay, with “Do you want to reconnect to the server?

Visual Studio locks up every time we try to check in or undo check out. More info. The issue appears to only happen when the user is connected via VPN from home. When he is in the office, the issue doesn't occur.